Chestertown, MD Homes for Sale

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  /20

  $169,885

  • 2 Beds
  • 1 Bath
  • 910 Sq Ft

  132 Prospect St, Chestertown, MD 21620

  Beautifully Remodeled Two-Level Colonial Offering Timeless Charm and Modern Comfort. This home features a Brand New Kitchen with New Cabinets (2026), Quartz Counters, Stainless Steel Appliances (2026), and a Stylish Tile Backsplash. Enjoy Fully Updated Bathrooms, New Flooring Throughout, and Spacious Bedrooms Filled With Natural Light. New Modern Lighting (2026) and Fresh Custom Paint enhance the

  Matthew Altizer ANR Realty, LLC

  132 Prospect St, Chestertown, MD 21620
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  /26

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,666 Sq Ft

  127 Wood Duck Ln, Chestertown, MD 21620

  Tom Riccio RE/MAX Point Realty

  127 Wood Duck Ln, Chestertown, MD 21620
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  /22

  $1,099,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,784 Sq Ft

  25 Landing Ln, Chestertown, MD 21620

  **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

  Julia Hilfiker Gunther-McClary Real Estate

  25 Landing Ln, Chestertown, MD 21620
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  /23

  $849,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,980 Sq Ft

  104 Little Harbor Way, Chestertown, MD 21620

  **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

  Julia Hilfiker Gunther-McClary Real Estate

  104 Little Harbor Way, Chestertown, MD 21620
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  /8

  $90,000

  • Land
  • 3.92 Acres
  • $22,959 per Acre

  0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

  Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. The rear portion of the property is designated forested shrub wetlands, though it’s been

  Maryn LeClair Chesapeake Real Estate Associates, LLC

  0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
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  /2

  $29,000

  • Land
  • 1.05 Acres
  • $27,619 per Acre

  206 Burchard Sawmill Rd, Chestertown, MD 21620

  Rare opportunity to own 1.05-Acre Vacant Land in Chestertown, MD! Located at 206 Burchard Sawmill Rd. Surrounded by natural beauty and close to local amenities, this lot provides both privacy and convenience. Don’t miss out on this rare chance to own land in historic Chestertown! The property sell AS IS. Buyer will need to verify zoning and utilities.

  Norman Domingo XRealty.NET LLC

  206 Burchard Sawmill Rd, Chestertown, MD 21620
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  /20

  $200,000

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  117 N Water St Unit 1B, Chestertown, MD 21620

  117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

  Liddy Campbell TTR Sotheby's International Realty

  117 N Water St Unit 1B, Chestertown, MD 21620
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  /2

  $38,000

  • Land
  • 0.34 Acre
  • $111,765 per Acre

  0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

  Dee Dee Miller Long & Foster Real Estate, Inc.

  0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

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